54582-35-3

74295-89-9

54582-35-3

GENERAL METHODS: N-(4-methoxybenzyl)cyanamide (1.0 mmol), glyoxime (2.0 mmol), cerium oxide nanoparticles (5.0 mol%) and anhydrous ethanol (5 mL) were sequentially added to a 25 mL round-bottomed flask equipped with a magnetic stirrer. The reaction mixture was heated to reflux under nitrogen protection with continuous stirring for 2 hours. After completion of the reaction, it was cooled to room temperature, filtered to remove the solid catalyst, and the filter cake was washed with anhydrous ethanol. The filtrates were combined and concentrated under reduced pressure to remove the solvent. The recovered catalyst was washed with dichloromethane and dried for 2 h. The catalyst was reused. The crude product was purified by column chromatography. All the compounds obtained from the isolation were characterized by melting point determination, infrared spectroscopy, NMR hydrogen spectroscopy, NMR carbon spectroscopy and elemental analysis. The physical data (melting point, IR spectra, NMR spectra) of the known compounds are in agreement with literature reports.